House holiday rentals in Lakeside

4.97 out of 5 average rating, 316 reviews

Home in Ramona

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

A contemporary casita is set against a vibrant sunset, showcasing large windows that reflect the warm colors of the sky. The entrance features a clear path leading to a well-lit doorway, surrounded by natural landscaping and scenic hillside views.

4.94 out of 5 average rating, 120 reviews

San Diego Casita for 6 Morey de Prieto Surf Ranch

The Morey de Prieto Surf Ranch is truly awesome! Reserve your stay in this 2 Bed/1 Bath 650 sq. ft. casita for six. Home includes a kitchen with a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, mixer for drinks, sink with prep trays, Moen faucet fixtures, gorgeous shower, Krups coffee maker, 50" smart TV equipped with WiFi and NetFlix, mountain views, workspace and a sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

4.97 out of 5 average rating, 887 reviews

An open-concept living area is highlighted by high ceilings and large windows, offering natural light. A modern kitchen features wood cabinets and a white island, while a dining table with turquoise chairs accommodates several guests. A cozy seating area is visible in the background.

Home in Ramona

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

4.96 out of 5 average rating, 106 reviews

A spacious studio features a purple sofa and a queen bed, both adorned with soft blankets and decorative pillows. Vibrant area rugs cover the wooden floor. Natural light floods the room through glass doors, leading to a private patio surrounded by greenery.

Home in San Diego

XLarge Artist Garden Suite w/Private Patio/Parking

*Forget your worries in this beautiful 700sq/ft spacious and serene space. *Come soak up in the artsy feel of this newly renovated large guest suite, ideally located in the middle of town close to SDSU. Roll out of bed and Enjoy a cup of coffee in the private patio then explore ALL of the city’s top attractions a short drive away. This beautiful space is clean, crisp and fully decorated with great style uniquely curated with original art by one of SD’s most established artists. * Enjoy*

A view into a modern living space reveals a sleek kitchen with bar seating and a spacious dining area. Natural light floods the room through large glass doors, showcasing lush greenery outside. A cozy area is completed with a colorful rug beneath and a inviting seating arrangement.

4.94 out of 5 average rating, 234 reviews

Cottage in the Garden! New! Modern!

COTTAGE IN THE GARDEN - New! Modern! Find beauty and serenity in this special guest house in one of San Diego's most desirable areas! Flowering bushes, plants, olive tree and fruit trees seen from all windows. All amenities: WiFi, Cable, serving dishes and tableware, full coffee bar, Ninja Blender, Flat screen TVs, 100% Egyptian Cotton Sheets or Boll and Branch Sheets (used by 3 Presidents), Japanese Toilette and more. 15 minutes to Downtown San Diego and 20 minutes to the beach!

A welcoming living area features a spacious beige sectional sofa adorned with patterned throw pillows. Natural light filters through a large window, complemented by soft, flowing curtains. A dark ottoman with decorative details adds a contrasting element to the cozy space.

4.97 out of 5 average rating, 120 reviews

Zen Retreat: 3-Bedroom Oasis near La Mesa Village

Relax in this charming 3-bedroom, 1-bathroom home located just 1 mile from the heart of Historic Downtown La Mesa Village. Nestled in a quiet, central neighborhood, this cozy retreat offers easy access to major freeways, top-rated restaurants, and the local trolley line making it a breeze to explore the best of San Diego. Within 10 to 15 miles, you’ll find yourself in iconic destinations like Downtown San Diego, Balboa Park, Coronado Island, scenic beaches, and beautiful mountain trails.

A colorful studio space features turquoise walls and a ceiling fan. A comfortable sofa with decorative pillows is paired with a coffee table. A bed with a floral-patterned comforter sits against a window, while a TV and white refrigerator complete the modern setup.

4.98 out of 5 average rating, 310 reviews

SDCannaBnB #2 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental! Our studio is newly remodeled with luxury ammenities. We proudly cater to the cannabis community and non-users alike. Our studio has HEPA air purifiers, is fully ventilated and receives deep cleanings between each guest. This ensures that every guest checks into a clean, fresh-smelling place that feels like home. Our studio is located in our quiet, fully fenced in backyard, close to San Diego's attractions

4.93 out of 5 average rating, 101 reviews

A charming exterior of a single-story home is showcased, surrounded by lush palm trees and vibrant landscaping. The front entrance features a round window and an archway, while the driveway is paved, offering easy access to the front door.

Home in Linda Vista

Guest Room with Beautiful Views

Welcome to our charming retreat nestled in San Diego. This private suite, attached to the main house, features its own bathroom, kitchenette, and a convenient private entrance with easy self-check-in. Just 10 minutes from Mission Beach, downtown San Diego, Balboa park, and SeaWorld. 5 min from Fashion Valley Mall, and only 2 minutes from the University of San Diego. You can either use the free parking space in front of the house or make use of the private driveway next to the house.

4.97 out of 5 average rating, 107 reviews

The kitchen features modern appliances, including a stainless steel refrigerator and gas stove. White cabinetry and a marble countertop enhance the sleek design. Ample storage options are visible, complemented by natural light entering through a window. A coffee maker and utensils are neatly arranged.

Home in Midway District

Dune’s Desert Oasis

Enjoy access to everything in San Diego from this centrally located home. Located in the midway district only four blocks from Sports Arena. This brand new unit is equipped with everything you need and more. It has a fully equipped kitchen with tons of storage, large living area, large bedroom, super fast Wi-Fi, filtered shower, backlit vanity mirror, full-size washer and dryer in closet, dimmable lighting throughout, cozy bedding, thick towels, parking, and tons of natural light.

4.92 out of 5 average rating, 129 reviews

Home in Kensington

Stylish 1Br Retreat: Parking AC Close 2 Everything

HIGHLIGHTS -Close to SD's main attractions -Stylish and comfy interior w/great lighting -Quaint, walkable neighborhood -Fully renovated kitchen w/new appliances -A/C -Washer/Dryer -Courtyard Patio -1 large, reserved parking spot Enjoy top tier restaurants, cafes and shops along vibrant Adams Ave or explore San Diego’s major attractions less than 15 min away. Downtown for Gaslamp; Balboa Park for museums and Zoo; SDSU for events and games; Mission Beach for fun in the sun.

4.96 out of 5 average rating, 144 reviews

The inviting entrance features a covered porch adorned with a vibrant yellow door. Succulents and greenery enhance the landscape, complemented by a palm tree nearby. The porch area includes seating, providing a welcoming atmosphere for relaxation.

Home in San Diego

The Cozy Craftsman

Escape to this serene, stylish retreat. Built in 1935, this Craftsman-style home exudes timeless San Diego charm. Perfectly situated in University Heights, bordering Hillcrest and North Park, you’ll be close to restaurants, cafés, grocery stores, public transportation, the San Diego Zoo, and Balboa Park. This 650 sq ft home has been renovated inside and out, and equipped with everything you need for a comfortable stay!

4.98 out of 5 average rating, 488 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.

Popular amenities for house rentals in Lakeside

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

4.89 out of 5 average rating, 197 reviews

The Queen House

Home in University Heights

A well-lit bedroom features a spacious bed with neutral bedding and striped pillows. Natural light enters through glass doors leading to a semi-private patio. A textured area rug and a potted plant add subtle warmth to the wood flooring.

4.86 out of 5 average rating, 101 reviews

Cozy University Heights Cottage

4.87 out of 5 average rating, 106 reviews

Entertainers Dream Pool Home

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

4.85 out of 5 average rating, 232 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

Superhost

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

Home in Lake Murray

4.88 out of 5 average rating, 216 reviews

Bright and spacious home with views, pool & spa.

4.81 out of 5 average rating, 128 reviews

The outdoor area showcases a clear pool surrounded by a spacious patio. Lounge chairs, a poolside table, and an umbrella are positioned for relaxation. The backdrop features low landscaping with cacti and a glimpse of the house, enhancing the tranquil setting.

Home in Lake Murray

Mid-Century Modern and Contemporary House

Home in San Pasqual Valley

An outdoor seating area is equipped with comfortable chairs surrounding a modern fire pit, where flames flicker gently. The pool glistens nearby, framed by lush landscaping and a serene hillside, with a light hue of sunset in the background.

4.96 out of 5 average rating, 157 reviews

Stunning 3 bedroom w/Views! Game Room/Pool/Hot Tub

4.97 out of 5 average rating, 104 reviews

An aerial view of the estate shows a sprawling layout with a swimming pool and outdoor leisure areas. A basketball court is visible beside the home, surrounded by lush greenery and landscaped gardens. The arrangement of buildings and paths creates an inviting outdoor space.

Home in Ramona

Retreat:GameRoom/PuttGreen/Volleyball/Pool/HotTub

Weekly house rentals

Home in Greater North Park

The living room features a comfortable sectional couch alongside a grey armchair and two soft ottomans. A round wooden coffee table is centered on a textured rug, showcasing a vase, candles, and books. A flat-screen TV and ceiling fan enhance the cozy atmosphere.

4.99 out of 5 average rating, 84 reviews

Boutique Balboa Park: Zoo & Downtown +FirePit

4.93 out of 5 average rating, 15 reviews

Lakeside Luxury-Panoramic Paradise

5 out of 5 average rating, 64 reviews

Not Quite Perfect

4.95 out of 5 average rating, 20 reviews

Helix Haven

5 out of 5 average rating, 36 reviews

Farmhouse on Sunny Outdoor Dining area 20min to SD

A private deck features a small round table surrounded by two blue chairs, situated under a palm tree. The view includes rolling hills and a clear blue sky with scattered clouds, offering a peaceful outdoor space to enjoy the scenery.

4.96 out of 5 average rating, 27 reviews

Studio In Home with Private Entry

5 out of 5 average rating, 29 reviews

San Diego retreat 4 Bd/Bath/Pool/Putting/Hot tub

An inviting outdoor space features a large hot tub, surrounded by lush greenery and spots for seating. A fire pit surrounded by comfortable seating is visible, complemented by dining options beneath umbrellas. The space is gently illuminated by soft lighting, creating a cozy atmosphere.

4.96 out of 5 average rating, 54 reviews

The Sand House-Cozy 3BR 2BA-HotTub+FirePit+Yard+EV

Private house rentals

5 out of 5 average rating, 14 reviews

BIG Modern Mt Helix Home with Pool

5 out of 5 average rating, 21 reviews

The exterior view of the home displays a warm-toned facade with a welcoming front door. A pathway of pavers leads to the entrance, bordered by mulch. Grass is maintained around the patio area, which features a compact seating arrangement with a small table and chairs.

Home in El Cajon

Cozy 1BR Home with Lovely Front Yard

The living room is furnished with a comfortable loveseat and a coffee table, complemented by a white TV stand supporting a large smart TV. Decorative plants and slender white branches enhance the ambiance, while soft lighting is provided by a standing lamp. Framed artwork adorns the walls.

4.98 out of 5 average rating, 60 reviews

Discover La Mesa: Your Perfect Cozy Base

4.98 out of 5 average rating, 81 reviews

A serene pool area is framed by vibrant green foliage and terracotta walls, with lounge chairs positioned nearby. Majestic mountains rise in the background under a clear blue sky. A shaded picnic table is visible, inviting relaxation in a tranquil outdoor setting.

Home in Jamul

Jamul Hacienda | Couples Retreat | Pool & Views!

5 out of 5 average rating, 13 reviews

A sunlit bedroom features a spacious queen bed adorned with decorative bedding and a light throw. A minimalist bench sits at the foot of the bed, while a desk and lamp occupy a corner. Windows provide natural light, illuminating the soft-toned walls.

Home in El Cajon

Cozy quiet getaway, great mattress (1-br)

4.9 out of 5 average rating, 10 reviews

*New La Mesa Escape – Private Studio

Superhost

The living area is accented with wooden beams and features a cozy sofa, an armchair, and a round wooden coffee table. Natural light fills the room through a window, with a piece of abstract artwork displayed on the wall, enhancing the inviting space.

4.88 out of 5 average rating, 25 reviews

Lakeside Haven | Mountain Views, Private Pool